supporting information-4 - rsc.org file1 supporting information-4: scaffold diversity -oriented...
TRANSCRIPT
1
Supporting Information-4:
Scaffold diversity-oriented synthesis of limonoid dimers: discovery of an axially chiral agent with in vivo anti-breast cancer activity
Wan-Shan Li,‡a Yang Yang,‡b Jun-Jun Liu,d Li Shen,*a Zhi Shi,*b and Jun Wu*c
a Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, P. R. China
b Department of Cell Biology & Institute of Biomedicine, National Engineering Research Center of Genetic Medicine, Guangdong Provincial Key Laboratory of Bioengineering Medicine, College of Life Science and Technology, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, P. R. China
c School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, P. R. China
d School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China
‡ These authors contributed equally
Copies of HRESIMS, UV, IR, 1D and 2D NMR spectra of compounds 5a, and 5b
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2018
2
Table of Contents: (Page)
1. HR-ESIMS for compound 5a·································································3-4 2. UV spectrum for compound 5a in CH3CN······································································5 3. IR spectrum for compound 5a·····················································································6 4. 1H NMR (400 MHz) spectrum of compound 5a in CDCl3·································7-10
5. 13C NMR (100 MHz) spectrum of compound 5a in CDCl3 ································11-15
6. DEPT135 (100 MHz) spectrum of compound 5a in CDCl3 ·······························16-20 7. 1H-1H COSY (400 MHz) spectrum of compound 5a in CDCl3 ···························21-22 8. HSQC (400 MHz) spectrum of compound 5a in CDCl3 ···································23-27 9. HMBC (400 MHz) spectrum of compound 5a in CDCl3 ···································28-34 10. NOESY (400 MHz) spectrum of compound 5a in CDCl3 ································35-39 11. HR-ESIMS for compound 5b·································································40-41 12. UV spectrum for compound 5b in CH3CN····································································42 13. IR spectrum for compound 5b···················································································43 14. 1H NMR (400 MHz) spectrum of compound 5b in CDCl3·································44-47
15. 13C NMR (100 MHz) spectrum of compound 5b in CDCl3 ································48-52
16. DEPT135 (100 MHz) spectrum of compound 5b in CDCl3 ·······························53-56 17. 1H-1H COSY (400 MHz) spectrum of compound 5b in CDCl3 ···························57-59 18. HSQC (400 MHz) spectrum of compound 5b in CDCl3 ···································60-64 19. HMBC (400 MHz) spectrum of compound 5b in CDCl3 ··································65-72 20. NOESY (400 MHz) spectrum of compound 5b in CDCl3 ································73-76 21. IR spectrum for compound 2a···················································································77 22. IR spectrum for compound 2b···················································································78
3
HR-ESIMS for compound 5a
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
4
HR-ESIMS for compound 5a
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
7
1H NMR (400 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
8
1H NMR (400 MHz) spectrum of compound 5a in CDCl3
H-2
1/H
-21'
H
-23/
H-2
3'
H-2
2/H
-22'
H-1
7/H
-17'
H-6
/H-6
'
H-3
/H-3
'
H3-
31/H
3-31
'
30-O
H/3
0'-O
H
2-O
H/2
'-OH
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
9
1H NMR (400 MHz) spectrum of compound 5a in CDCl3
H-3
3/H
-33'
H
3-37
/ H3-
37'
H-9
/ H-9
'
Hβ-
11/Hβ-
11'
Hα-
11/Hα-
11'
H-5
/H-5
' H
a-29
/Ha-
29'
Hb-
29/H
b-29
'
6-O
H/6
'-OH
Acetone
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
Hβ-
12/Hβ-
12'
H3-
19/H
3-19
'
H3-
35/H
3-35
' H
3-34
/H3-
34'
H3-
28/H
3-28
'
H3-
38/H
3-38
' H
3-39
/H3-
39'
H3-
18/H
3-18
' Hα-
12/Hα-
12'
1H NMR (400 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
13C NMR (100 MHz) spectrum of compound 5a in CDCl3
11
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
12
13C NMR (100 MHz) spectrum of compound 5a in CDCl3
C-3
0/C
-30'
C-3
2/C
-32'
C-7
/C-7
' C
-36/
C-3
6'
C-1
6/C
-16'
C-2
3/C
-23'
C
-21/
C-2
1'
C-1
4/C
-14'
C-8
/C-8
'
C-2
0/C
-20'
C-2
2/C
-22'
C-1
5/C
-15'
C-1
/C-1
' C
-3/C
-3'
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
13
13C NMR (100 MHz) spectrum of compound 5a in CDCl3
C-1
7/ C
-17'
C-2
/C-2
'
C-6
/C-6
'
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
14
13C NMR (100 MHz) spectrum of compound 5a in CDCl3
C-1
3/C
-13'
C-3
3/C
-33'
C-1
2/C
-12'
C-3
7/C
-37'
C-3
1/C
-31'
C-1
0/C
-10'
C-9
/C-9
'
C-5
/C-5
'
C-4
/C-4
'
C-2
9/C
-29'
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
15
13C NMR (100 MHz) spectrum of compound 5a in CDCl3
C-3
4/C
-34'
C-3
9/C
-39'
C-2
8/C
-28'
C-3
8/C
-38'
C
-11/
C-1
1' C-3
5/C
-35'
C-1
8/C
-18'
C-1
9/C
-19'
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
16
DEPT135 (100 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
17
DEPT135 (100 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
18
DEPT135 (100 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
19
DEPT135 (100 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
20
DEPT135 (100 MHz) spectrum of compound 5a in CDCl3
1'
2'3'
4'
5'6'7'
8'
9'10'
11' 12'
13'
14'15'
16'
17'
18'19'
20' 21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
1415
16
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OH OH
MeOO
O
Me
H
HO HH
3637
38
39
OMe
Me
OMe
Me36'37'38'
39'
O32
33
34
35Me
Me
MeMe O
32'
33'35'
34'
40
HR-ESIMS for compound 5b
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
HR-ESIMS for compound 5b
41
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
44
1H NMR (400 MHz) spectrum of compound 5b in CDCl3
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
45
1H NMR (400 MHz) spectrum of compound 5b in CDCl3
H-2
1/H
-21'
H
-23/
H-2
3'
H-2
2/H
-22'
H-1
7/H
-17'
H-6
/H-6
' H-3
/H-3
'
H3-
31/H
3-31
'
30-O
H/3
0'-O
H 1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
46
1H NMR (400 MHz) spectrum of compound 5b in CDCl3
H-3
3/H
-33'
H3-
37/ H
3-37
' H
-9/ H
-9'
Hα-
11/Hα-
11'
H-5
/H-5
' H
a-29
/Ha-
29'
Hb-
29/H
b-29
'
6-O
H/6
'-OH
2-O
H/2
'-OH
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
47
1H NMR (400 MHz) spectrum of compound 5b in CDCl3
Hβ-
12/Hβ-
12'
H3-
19/H
3-19
'
H3-
35/H
3-35
'
H3-
34/H
3-34
'
H3-
28/H
3-28
'
H3-
38/H
3-38
' H
3-39
/H3-
39'
H3-
18/H
3-18
' Hα-
12/ Hα-
12'
Hβ-
11/Hβ-
11'
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
13C NMR (100 MHz) spectrum of compound 5b in CDCl3
48
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
49
13C NMR (100 MHz) spectrum of compound 5b in CDCl3
C-3
0/C
-30'
C-3
2/C
-32'
C-7
/C-7
' C
-36/
C-3
6'
C-1
6/C
-16'
C-2
3/C
-23'
C
-21/
C-2
1'
C-1
4/C
-14'
C-8
/C-8
'
C-2
0/C
-20'
C-2
2/C
-22'
C-1
5/C
-15'
C-1
/C-1
' C
-3/C
-3'
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
50
13C NMR (100 MHz) spectrum of compound 5b in CDCl3
C-1
7/ C
-17'
C-2
/C-2
'
C-6
/C-6
'
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
51
13C NMR (100 MHz) spectrum of compound 5b in CDCl3
C-1
3/C
-13'
C-3
3/C
-33'
C-1
2/C
-12'
C-3
7/C
-37'
C-3
1/C
-31'
C-1
0/C
-10'
C-9
/C-9
'
C-5
/C-5
'
C-4
/C-4
'
C-2
9/C
-29'
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
52
13C NMR (100 MHz) spectrum of compound 5b in CDCl3
C-3
4/C
-34'
C-3
9/C
-39'
C-2
8/C
-28'
C-3
8/C
-38'
C-1
1/C
-11'
C-3
5/C
-35'
C-1
8/C
-18'
C-1
9/C
-19'
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
DEPT135 (100 MHz) spectrum of compound 5b in CDCl3
53
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
54
DEPT135 (100 MHz) spectrum of compound 5b in CDCl3
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
55
DEPT135 (100 MHz) spectrum of compound 5b in CDCl3
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'
56
DEPT135 (100 MHz) spectrum of compound 5b in CDCl3
1'
2'3'
4'
5'6' 7'
8'
9' 10'
11'12'
13'
14'15'
16'
17'
18' 19'
20'21'
22'23'
28'
29'
30'
31'
1
23
4
567
8
910
11 12
13
14
1516
17
1819
20 21
2223
28
29
30
31
O
MeO
O
O
Me
OH OH
H
MeOO
O
Me
H
HO H
O
MeO
O
O
Me
OHHO
OMeO
O
Me
H
OHH H
O
Me Me
36
3738
39 O
Me Me36'
37'38'
39'
O32
33
34
35Me
Me
MeMeO
32'
33' 35'34'